This has been a big problem for my team, I feel our holds are perfectly okay, but for now I'll focus on what we're doing for even uber/player pushes trying to take the point.
Generally we've just been buffing demo, pocket and roamer and jumping them in, but I feel that's been entirely ineffective and even really getting a pick seems to not happen the majority of the time, it was suggested that we fully buff the roamer first, and he initiates the push, rather than our med building uber in spawn we push him forward a bit, but try and avoid putting him in a position where he's just going to get forced. With this the roamer tries to force uber or pick demo/med, and the rest of the team follows in after, presumably buffed.
Are there any huge problems with this strategy? Any other, alternative suggestions a lower division team would be capable of pulling off without something situational like a sniper medic pick?

No Mercy

If you are committing to a push then suiciding your roamer to force them to pop uber first is not a good idea. It is difficult to make effective use of ubers on viaduct if your enemy is conscious of not bunching up and giving the uber vulnerable targets. Typically the team with more players alive once ubers have traded will be victorious.

Generally speaking scouts picks are the key* (at div6 level i dont know it this maxim holds true though, aim maybe scouts cant aim) and having 1 or 2 more scouts than your opponent is enough to overwhelm your opponent by walking forward and pressuring from both sides. Of course dememen and medics remain more valuable, but practically they should not be a easy target most of the time, and it is not worth 2-for-1ing yourself for one of these picks.

What you should be doing to find some advantage/room to push forward:

1. Free kills: look for opportunities to kill over extended noobs who think b-lining the medic or hiding in fancy spots behind is the key to success.

2. Damage Attrition: Pocket your demoman and try and long range spam their combo back while you slowly take territory looking out for sticky traps. Often this will eventually induce one of their scouts or soldiers to try and bomb onto you in which case backup, focus on killing the bomber without losing anyone, and then you have a real advantage.

3. Profitable trades: This pretty much means if the soldier see a chance to get a sure kill on anything he should take it, at the cost of his life. Same holds true for a scout on a demoman/medic. The key here is sure. The risk for return is worth it but if you fail our whole team needs to dick around waiting for you to respawn. Even equal class trades (scout for scout etc) are worth it due to the nature of the respawn timer being much shorter on attack.

Aggressive flanking play is often a good option. If you can leak players behind while still applying forward pressure from the demo/combo, pincering the enemy combo will lead to some wipes (6 downs) and a free capture point. Soldiering controlling the highground behind the enemy is very strong, and most 'bombing' soldiers should be very aware of this area as an excellent landing point for their jumps. Bombing soldier != suiciding soldier if done correctly. This is a key difference between good and bad roamers (and pockets, who can often follow in on the action on this map).

Note: is it common for teams to want to wait for uber until they push, even if this gives the other team uber also. This is a defensible decision, but ultimately a poor choice / crux for bad coordination and medic awareness. It is wasting time, at the CP point clock is ticking. If playing correctly, you want to take every equal advantages opportunity to pressure as a whole team. A good medic will be able to balance providing combat healing / grinding while fighting without compromising his own position to allow bombers and flankers to kill him. Yes i realise this is unlikely at a div6 level (or even low div1 level). That said if you've had real success with suiciding your whole team while a scout/medic grinds uber then keep going for it. Just remeber you are giving your opponents a free 20-30 seconds of time on point in this attempt to find an advantage.

TLDR:
1. Team with more people alive can hold the point.
2. Therefore: Without point get kills (with point don't trade kills).
3. Any kill is about as good as any other so target vulnerable enemies, NOT "key" targets.

No Mercy

I'm assuming scout picks are actually quite important, especially pushing, as it allows our scouts to roam free (more or less) and dish out some damage without having to deal with 1v1's?

Quote:

Originally Posted by Ask A Question Forum

So, if I'm parsing this correctly, you focus out of position players, and slowly, relatively speaking, win a war of attrition on the point due to faster spawns on attacking side rather than defending? In massive tl;dr terms anyway.

As for demo not being pocketed, just buff him and heal him when he needs it, and pocket the pocket as per usual? Is there any particular reason for this? (I'm 95% sure there is, but I don't know *what*) I'd be assuming with my train of thought that you'd want to focus on keeping the demo alive due to the sheer amount of spam he puts out, so pocket him, but this is also likely due to our demoman having an awful habit of overaggression. That's probably altered my thought train a lot, I guess I can see it working with a less aggro demoman who doesn't end up eating the ground like the roamer on a regular basis.

No Mercy

Like any map, any kill is good (especially because of respawn times on this map), so getting a kill fast by isolating some forward player is a big plus. A lot of the time it isn't "slow" and you can just force them off the point quickly with your sheer damage and presence (check out our viaduct games where I have played pocket OR demo, the one I played scout vs FRAY is to a lesser degree but still applies I guess).

It's not your demoman that needs to push forward and get ground - it's your pocket.

No Mercy

The problem lies mostly in the execution of the aforementioned shitfight, would we just solo-uber pocket in, demo spams from further back on one of the sides and everyone else just spams in from height advantageous location, waiting for the even ubers to fade, then move in to cleanup/cap/take ground? Sorry if this all seems like basic stuff to you guys, but I guess that's what ask-a-question is for.

No Mercy

It's pretty hard to explain what you are meant to do in an uber. It is very situational most of the time, but I guess a basic way to put it would be:

-if bunched, uber pocket into enemy team
-force multi uber on other side
-attempt to get any kill (it could be on the combo, or even a scout or roamer, doesn't matter)
-all the while your team is avoiding damage as much as they can since you don't want to multi uber (ideally!)
-after uber team gets overheals and +forwards (health advantage + IDEALLY player advantage)

No Mercy

So optimally with ubers you're looking to not have to multi at all except in specific situations/pushes, and in the viaduct context you'd just want to try and spam everyone possible to force heaps of multi-ing, meaning you'll have uber over theirs for a few more seconds, meaning you can chase the medic or cleanup, whatever their positioning entails? Hopefully you don't let their med get away so you can milk uber advantage for time on the point, correct?

To continue on from that, in what circumstances would you avoid chasing the medic, assuming sufficient players are up to protect your own and the enemy is falling out with maybe 1 soldier/scout + med (Pertaining to this particular viaduct push, I think I'm understanding the push itself at a basic level now, I feel the shitfight understanding will come with time and experience)